EREMOMYCIN - NEW GLYCOPEPTIDE ANTIBIOTIC: CHEMICAL PROPERTIES AND STRUCTURE

By a combination of chemical and spectroscopic (1H and 13C NMR) studies the structure of a glycopeptide antibiotic eremomycin has been elucidated. It is closely related to vancomycin, but differs in sugar and chlorine content. The eremomycin aglycone contains monodechlorovancomycinic acid; the only...

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Bibliographic Details
Published in:Journal of antibiotics 1989/12/25, Vol.42(12), pp.1790-1799
Main Authors: GAUSE, GEORGE F., BRAZHNIKOVA, MARIYA G., LOMAKINA, NINA N., BERDNIKOVA, TATIANA F., FEDOROVA, GALINA B., TOKAREVA, NINA L., BORISOVA, VALERIYA N., BATTA, GYULA Y.
Format: Article
Language:English
Subjects:
2,3,6-trideoxy-3-amino-C-3-methyl-L-arabino-hexopyranose
Anti-Bacterial Agents
Antibacterial agents
antibiotics
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimicrobial Cationic Peptides
Biological and medical sciences
Chemical Phenomena
Chemistry
eremomycin
Glycopeptides
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Sequence Data
N.M.R
Peptides
Pharmacology. Drug treatments
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
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Summary:By a combination of chemical and spectroscopic (1H and 13C NMR) studies the structure of a glycopeptide antibiotic eremomycin has been elucidated. It is closely related to vancomycin, but differs in sugar and chlorine content. The eremomycin aglycone contains monodechlorovancomycinic acid; the only chlorine atom is situated in the second amino acid after the N-terminal amino acid residue of the peptide. The sugar part is composed of glucose and two residues of an amino sugar shown to be 2, 3, 6-trideoxy-3-amino-C-3-methyl-L-arabino-hexopyranose (4-epi-vancosamine). One of the amino sugar residues is a component of the disaccharide 2-O-(α-L-4-epi-vancosaminyl)-β-Dglucopyranose, attached to a triphenyl ether moiety; the position of another one is at the serine oxygen in the C-terminal region of the aglycone.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.42.1790